Aniline → 2-chloro-N-phenylquinazolin-4-amine

HRID 429015

Reaction equation

HRID 429015 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)C>[Cl:1][C:2]1[N:11]=[C:10]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2528862,4-Dichloroquinazoline

Product 1

HCID 3179082-chloro-N-phenylquinazolin-4-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2,4-dichloro-quinazoline (15 g), N,N-diisopropyl-ethylamine (24.9 ml) and aniline (7.5 ml) in isopropanol (75 ml) is heated to reflux for 45 min. The cold reaction mixture is filtered and the filtrate is concentrated in vacuo. The residue is crystallized from diethylether-toluene (1:1) to give 2-chloro-4-phenylamino-quinazoline, m.p. 194-196° C.

Workup

  1. temperatureto reflux for 45 min
  2. customThe cold reaction mixture
  3. filtrationis filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customThe residue is crystallized from diethylether-toluene (1:1)

Sources & evidence

ORD record
ord-ce3ea6161b1e453eb066c585f6a0c5fe
Source dataset
uspto-grants-2001_11
Patent number
US06316203B1

Linked notes

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